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Benjamin was a part of a flight of angels led by Ishim that included himself, Mirabel, Castiel and two other unnamed angels. In
1901, Ishim took his flight to Orono, Maine where he claimed that the angel Akobel had fathered a Nephilim with Lily Sunder and had to die along with his daughter, May. Confronting Akobel, after Mirabel blocked a blow aimed at Ishim with an angel blade, he hold Akobel so Castiel could recite his crime and punishment and Mirabel could kill him. Benjamin stayed outside with the rest of the flight as Ishim went to kill the Nephilim alone.

Benjamin with his flight in 1901.

Over the next century, Castiel eventually left the flight to command his own. Like the rest of the angels, Benjamin was expelled fromHeaven and lost use of his wings as a result. Like most of his flight, Benjamin retained his old vessel and communicated with the her as they were more than vessel and angel, they were friends. While playing a game, Benjamin was attacked by Lily Sunder, who was out for revenge. Benjamin sent out a distress signal before being killed by Lily. He was the third member of his flight to die by her hands.

Benjamin is the second angel shown to interact with his vessel while possessing it. The first was Lucifer, while he was possessing Jefferson Rooney.

While Benjamin's vessel is in fact female, Benjamin himself is always referred to by male pronouns. This was noted by Dean Winchester who asked if Benjamin was a chick. Castiel explained that "Benjamin is an angel. His vessel is a woman."